Organic electronic element comprising compound for organic electronic element, and electronic device thereof

ABSTRACT

An organic electric element includes a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode. The organic material layer includes the compound represented by Formula 1. When the organic electric element includes the compound in the organic material layer, luminous efficiency, stability, and life span can be improved.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority from and the benefit under 35 U.S.C.§119(a) of Korean Patent Application No. 10-2013-0092419 filed on Aug.5, 2013, and Korean Patent Application No. 10-2014-0094452 filed on Jul.25, 2014, the contents of which are hereby incorporated by reference forall purposes as if fully set forth herein.

BACKGROUND

1. Technical Field

The present invention relates to compounds for organic electricelements, organic electric elements using the same, and electronicdevices thereof.

2. Background Art

In general, an organic light emitting phenomenon refers to a phenomenonin which electric energy is converted into light energy of an organicmaterial. An organic electric element utilizing the organic lightemitting phenomenon usually has a structure including an anode, acathode, and an organic material layer interposed therebetween. In manycases, the organic material layer may have a multilayered structureincluding multiple layers made of different materials in order toimprove the efficiency and stability of an organic electric element, andfor example, may include a hole injection layer, a hole transport layer,a light emitting layer, an electron transport layer, an electroninjection layer, or the like.

A material used as an organic material layer in an organic electricelement may be classified into a light emitting material and a chargetransport material, for example, a hole injection material, a holetransport material, an electron transport material, an electroninjection material, and the like according to its function.

Currently, the power consumption is required more than more as size ofdisplay becomes larger and larger in the portable display market.Therefore, the power consumption is a very important factor in theportable display with a limited power source of the battery, andefficiency and life span issue also be solved.

Efficiency, life span, driving voltage, and the like are correlated witheach other. For example, if efficiency is increased, then drivingvoltage is relatively lowered, and the crystallization of an organicmaterial due to Joule heating generated during operation is reduced asdriving voltage is lowered, as a result of which life span shows atendency to increase. However, efficiency cannot be maximized only bysimply improving the organic material layer. This is because long lifespan and high efficiency can be simultaneously achieved when an optimalcombination of energy levels and T1 values, inherent material properties(mobility, interfacial properties, etc.), and the like among therespective layers included in the organic material layer is given.

Further, in order to solve the emission problem with a hole transportlayer in a recent organic electric element, an emission-auxiliary layeris present between the hole transport layer and a light emitting layer,and it is time to develop different emission-auxiliary layers accordingto respective light emitting layers (R, G, B).

In general, an electron transferred from an electron transport layer toa light emitting layer and a hole transferred from a hole transportlayer to the light emitting layer are recombined to form an exciton.However, since a material used in a hole transporting layer should havea low HOMO value, it mainly has a low T1 value. Due to this, excitonsgenerated from a light emitting layer are transported to the holetransporting layer, resulting in a charge unbalance in the lightemitting layer. Thus, light emission occurs in the hole transportinglayer or at an interface of the hole transporting layer so that theorganic electroluminescent device is reduced in color purity,efficiency, and lifespan.

Also, when using a material having rapid hole mobility for reducing adriving voltage, this is tend to decrease the efficiency. In an OLEDs, acharge unbalance in the light emitting layer is caused because of thathole mobility is faster than electron mobility, and reduced efficiencyand lifespan is happened.

Therefore, an emitting auxiliary layer must be formed by a material whatcan solve the problems of an hole transport layer, having hole mobilityto give the suitable driving voltage, high T1 energy value and wide bandgap. These requirements are not satisfied only by structuralcharacteristics about a core of the emitting auxiliary layer's material.Therefore, it is necessary to develop of the material for the emittingauxiliary layer having high T1 energy value and wide band gap, toimprove efficiency and lifespan of the organic electric element ascombined core of material and characteristics of sub substituentsappropriately.

In order to allow an organic electric element to fully exhibit theabove-mentioned excellent features, it should be prerequisite to supporta material constituting an organic material layer in the element, forexample, a hole injection material, a hole transport material, a lightemitting material, an electron transport material, an electron injectionmaterial, an emitting auxiliary layer, or the like, by a stable andefficient material. However, such a stable and efficient organicmaterial layer material for an organic electric element has not yet beenfully developed. Accordingly, there is a continuous need to develop newmaterial of the emission-auxiliary layer, and material of the holetransport layer.

SUMMARY

In order to solve one or more of the above-mentioned problems occurringin the prior art, an aspect of the present invention is to provide anorganic electric element using a compound which allows an organicelectric element to have high luminous efficiency, low driving voltage,high heat-resistant, and to be improved in color purity and life span,and an electronic device including the organic electric element.

In accordance with an aspect of the present invention, there areprovided organic electric elements comprising a first electrode, asecond electrode, and a light emitting layer disposed between the firstelectrode and the second electrode, the organic electric elementcomprises an organic material layer disposed between the first electrodeand the light emitting layer, the organic material layer comprising acompound represented by the following Formula.

In another aspect of the present invention, there are providedelectronic devices including the organic electric elements.

By using the compound according to embodiments of the present invention,an organic electric element according to one or more embodiments of thepresent invention not only has high luminous efficiency, low drivingvoltage and high heat-resistant and, but can also be significantlyimproved in color purity, and life span.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 illustrates an example of an organic light emitting diodeaccording to an embodiment of the present invention.

DETAILED DESCRIPTION

Hereinafter, some embodiments of the present invention will be describedin detail with reference to the accompanying illustrative drawings.

In designation of reference numerals to components in respectivedrawings, it should be noted that the same elements will be designatedby the same reference numerals although they are shown in differentdrawings. Further, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif it is described in the specification that one component is“connected,” “coupled” or “joined” to another component, a thirdcomponent may be “connected,” “coupled,” and “joined” between the firstand second components, although the first component may be directlyconnected, coupled or joined to the second component. In addition, itwill be understood that when an element such as a layer, film, region orsubstrate is referred to as being “on” or “over” another element, it canbe directly on the other element or intervening elements may also bepresent. In contrast, when an element is referred to as being “directlyon” another element, there are no intervening elements present.

As used in the specification and the accompanying claims, unlessotherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term “halo” or “halogen” as used hereinincludes fluorine, chlorine, bromine, or iodine.

Unless otherwise stated, the term “alkyl” or “alkyl group” as usedherein has a single bond of 1 to 60 carbon atoms, and means aliphaticfunctional radicals including a linear alkyl group, a branched chainalkyl group, a cycloalkyl group (alicyclic), or an alkyl groupsubstituted with a cycloalkyl.

Unless otherwise stated, the term “haloalkyl” or “halogen alkyl” as usedherein includes an alkyl group substituted with a halogen.

Unless otherwise stated, the term “alkenyl” or “alkynyl” as used hereinhas, but not limited to, double or triple bonds of 2 to 60 carbon atoms,and includes a linear alkyl group, or a branched chain alkyl group.

Unless otherwise stated, the term “cycloalkyl” as used herein means, butnot limited to, alkyl forming a ring having 3 to 60 carbon atoms.

The term “alkoxyl group”, or “alkyloxy group” as used herein means anoxygen radical attached to an alkyl group, but not limited to, and has 1to 60 carbon atoms.

The term “aryloxyl group” or “aryloxy group” as used herein means anoxygen radical attached to an aryl group, but not limited to, and has 6to 60 carbon atoms.

Unless otherwise stated, the term “fluorenyl group” or “fluorenylenegroup” as used herein means, univalent or bivalent functional groupwhich R, R′ and R″ are all hydrogen in the structural formula below.Also, “substituted fluorenyl group” or “substituted fluorenylene group”means, functional group which at least any one of R, R′ and R″ is afunctional group other than hydrogen and spiro compound which R and R′can be linked together with the carbone to which they are attached toform spiro compound.

Unless otherwise stated, the term “aryl group” or “arylene group” asused herein has, but not limited to, 6 to carbon atoms. The aryl groupor arylene group means a monocyclic, ring assemblies, fused polycyclicsystem or spiro compound.

Unless otherwise stated, the term “heterocyclic group” as used hereinmeans, but not limited to, a non-aromatic ring as well as an aromaticring like “heteroaryl group” or “heteroarylene group”. The heterocyclicgroup as used herein means, but not limited to, a ring containing one ormore heteroatoms, and having 2 to 60 carbon atoms. Unless otherwisestated, the term “heteroatom” as used herein represents at least one ofN, O, S, P, and Si. The heterocyclic group means a monocyclic, ringassemblies, fused polycyclic system or spiro compound containing one ormore heteroatoms.

Also, the term “heterocyclic group” may include SO₂ instead of carbonconsisting of cycle. For example, “heterocyclic group” includes compoundbelow.

Unless otherwise stated, the term “ring” as used herein means, amonocyclic and polycyclic, an aliphatic ring and heterocyclic groupcontaining at least one heteroatom, and an aromatic ring and anon-aromatic ring.

Unless otherwise stated, the term “polycyclic” as used herein means,ring assemblies like biphenyl and terphenyl, fused polycyclic system andspiro compound, an aromatic ring and a non-aromatic ring, and analiphatic ring and heterocyclic group containing at least oneheteroatom.

Unless otherwise stated, the term “ring assemblies” as used hereinmeans, two or more cyclic systems (single rings or fused systems) whichare directly joined to each other by double or single bonds are namedring assemblies when the number of such direct ring junctions is oneless than the number of cyclic systems involved. The ring assembliesalso mean, same or different ring systems are directly joined to eachother by double or single bonds.

Unless otherwise stated, the term “fused polycyclic system” as usedherein means, fused ring type which has at least two atoms as the commonmembers, fused two or more aliphatic ring systems and a fused heteroring system containing at least one heteroatom. fused polycyclic systemis an aromatic ring, a hetero aromatic ring, an aliphatic ring, or thecombination of these.

Unless otherwise stated, the term “spiro compound” as used herein has, aspiro union which means union having one atom as the only common memberof two rings. The common atom is designated as ‘spiro atom’. Thecompounds are defined as ‘monospiro-’, ‘dispiro-’ or ‘trispiro-’depending on the number of spiro atoms in one compound.

Also, when prefixes are named subsequently, it means that substituentsare listed in the order described first. For example, an arylalkoxymeans an alkoxy substituted with an aryl, an alkoxylcarbonyl means acarbonyl substituted with an alkoxyl, and an arylcarbonylalkenyl alsomeans an alkenyl substitutes with an arylcarbonyl, wherein thearylcarbonyl may be a carbonyl substituted with an aryl.

Unless otherwise stated, the term “substituted or unsubstituted” as usedherein means that substitution is carried out by at least onesubstituent selected from the group consisting of, but not limited to,deuterium, halogen, an amino group, a nitrile group, a nitro group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkylamine group, aC₁-C₂₀ alkylthio group, a C₆-C₂₀ arylthio group, a C₂-C₂₀ alkenyl group,a C₂-C₂₀ alkynyl group, a C₃-C₂₀ cycloalkyl group, a C₆-C₆₀ aryl group,a fluorenyl group, a C₆-C₂₀ aryl group substituted by deuterium, aC₈-C₂₀ arylalkenyl group, a silane group, a boron group, a germaniumgroup, and a C₂-C₂₀ heterocyclic group containing at least oneheteroatom selected from O, N, S, Si, and P.

Otherwise specified, the Formulas used in the present invention are asdefined in the index definition of the substituent of the followingFormula.

Wherein, when a is an integer of zero, the substituent R¹ is absent,when a is an integer of 1, the sole R¹ is linked to any one of thecarbon atoms constituting the benzene ring, when a is an integer of 2 or3, the substituent R¹s may be the same and different, and are linked tothe benzene ring as follows. when a is an integer of 4 to 6, thesubstituents R¹s may be the same and different, and are linked to thebenzene ring in a similar manner to that when a is an integer of 2 or 3,hydrogen atoms linked to carbon constituents of the benzene ring beingnot represented as usual.

FIG. 1 illustrates an organic electric element according to anembodiment of the present invention.

Referring to FIG. 1, an organic electric element 100 according to anembodiment of the present invention includes a first electrode 120formed on a substrate 110, a second electrode 180, and an organicmaterial layer between the first electrode 120 and the second electrode180, which contains the inventive compound. Here, the first electrode120 may be an anode (positive electrode), and the second electrode 180may be a cathode (negative electrode). In the case of an invertedorganic electric element, the first electrode may be a cathode, and thesecond electrode may be an anode.

The organic material layer includes a hole injection layer 130, a holetransport layer 140, a light emitting layer 150, an electron transportlayer 160, and an electron injection layer 170 formed in sequence on thefirst electrode 120. Here, the layers included in the organic materiallayer, except the light emitting layer 150, may not be formed. Theorganic material layer may further include a hole blocking layer, anelectron blocking layer, an emission-auxiliary layer 151, a buffer layer141, etc., and the electron transport layer 160 and the like may serveas the hole blocking layer.

Although not shown, the organic electric element according to anembodiment of the present invention may further include at least oneprotective layer or one capping layer formed on at least one of thesides the first and second electrodes, which is a side opposite to theorganic material layer.

The inventive compound employed in the organic material layer may beused as a host material, a dopant material, or a capping layer materialin the hole injection layer 130, the hole transport layer 140, theelectron transport layer 160, the electron injection layer 170, or thelight emitting layer 150. For example, the inventive compound may beused as the hole transport layer 140, and/or the emission-auxiliarylayer 151.

Since depending on the type and position of a substituent to beattached, a band gap, electrical properties, interfacial properties, andthe like may vary even in the same core, it is very important what thetypes of core and a combination of substituent attached to the core are.Specially, long life span and high efficiency can be simultaneouslyachieved when an optimal combination of energy levels and T1 values,inherent material properties (mobility, interfacial properties, etc.),and the like among the respective layers included in the organicmaterial layer is given.

As already described above, in order to solve the emission problem witha hole transport layer in a conventional organic electric element, anemission-auxiliary layer is preferably formed between the hole transportlayer and a light emitting layer, and it is time to develop differentemission-auxiliary layers according to respective light emitting layers(R, G, B). However, even when a similar core is used, it is verydifficult to infer the characteristics of an emission-auxiliary layer ifa used organic material layer varies because the correlation between theemission-auxiliary layer and a hole transport layer and the correlationbetween the emission-auxiliary layer and a light emitting layer (host)mused be discovered.

Accordingly, in the present invention, a combination of energy levelsand T1 values, inherent material properties (mobility, interfacialproperties, etc.), and the like among the respective layers included inthe organic material layer is optimized by forming a hole transportlayer, and/or an emission-auxiliary layer by using the compoundrepresented by Formula 1, and thus the life span and efficiency of theorganic electric element can be improved at the same time.

The organic electric element according to an embodiment of the presentinvention may be manufactured using various deposition methods. Theorganic electric element according to an embodiment of the presentinvention may be manufactured using a PVD (physical vapor deposition)method or CVD (chemical vapor deposition) method. For example, theorganic electric element may be manufactured by depositing a metal, aconductive metal oxide, or a mixture thereof on the substrate to formthe anode 120, forming the organic material layer including the holeinjection layer 130, the hole transport layer 140, the light emittinglayer 150, the electron transport layer 160, and the electron injectionlayer 170 thereon, and then depositing a material, which can be used asthe cathode 180, thereon. Also, an emitting auxilary layer 151 may becomprised between the hole transport layer 140 and the light emittinglayer 150.

And also, the organic material layer may be manufactured in such amanner that a smaller number of layers are formed using various polymermaterials by a soluble process or solvent process, for example, spincoating, dip coating, doctor blading, screen printing, inkjet printing,or thermal transfer, instead of deposition. Since the organic materiallayer according to the present invention may be formed in various ways,the scope of protection of the present invention is not limited by amethod of forming the organic material layer.

According to used materials, the organic electric element according toan embodiment of the present invention may be of a top emission type, abottom emission type, or a dual emission type.

A WOLED (White Organic Light Emitting Device) readily allows for theformation of ultra-high definition images, and is of excellentprocessability as well as enjoying the advantage of being produced usingconventional color filter technologies for LCDs. In this regard, variousstructures for WOLEDs, used as back light units, have been, in the mostpart, suggested and patented. Representative among the structures are aparallel side-by-side arrangement of R (Red), G (Green), B (Blue)light-emitting units, a vertical stack arrangement of RGB light-emittingunits, and a CCM (color conversion material) structure in whichelectroluminescence from a blue (B) organic light emitting layer, andphotoluminescence from an inorganic luminescent using theelectroluminescence are combined. The present invention is applicable tothese WOLEDs.

Further, the organic electric element according to an embodiment of thepresent invention may be any one of an organic light emitting diode(OLED), an organic solar cell, an organic photo conductor (OPC), anorganic transistor (organic TFT), and an element for monochromatic orwhite illumination.

Another embodiment of the present invention provides an electronicdevice including a display device, which includes the above describedorganic electric element, and a control unit for controlling the displaydevice. Here, the electronic device may be a wired/wirelesscommunication terminal which is currently used or will be used in thefuture, and covers all kinds of electronic devices including a mobilecommunication terminal such as a cellular phone, a personal digitalassistant (PDA), an electronic dictionary, a point-to-multipoint (PMP),a remote controller, a navigation unit, a game player, various kinds ofTVs, and various kinds of computers.

Hereinafter, an organic electric element according to an aspect of thepresent invention will be described.

In accordance with an aspect of the present invention, there is providedan organic electric elements comprising a first electrode, a secondelectrode, and a light emitting layer disposed between the firstelectrode and the second electrode, the organic electric elementcomprises an organic material layer disposed between the first electrodeand the light emitting layer, the organic material layer comprising acompound represented by Formula 1.

In formula 1 above, each symbol may be defined as follows. In formula 1above, X and Y may be each independently O or S. For example, X and Ycan be all 0 or S, X is O and Y is S, or X is S and Y is O.

In formula 1 above, Ar¹ and Ar² may be each independently selected fromthe group consisting of a C₆-C₆₀ aryl group, a fluorenyl group andcombinations thereof. q is an integer of 1 or 2, and each of Ar¹ and Ar²may be the same or different when q is 2.

Preferably, Ar¹ and Ar² may be each independently a C₆-C₂₅ aryl group ora fluorenylene group, also preferably, C₆, C₁₀, C₁₂ aryl group, and morepreferably, substituted or unsubstituted with naphthyl phenyl group,naphthyl group, biphenyl group, substituted or unsubstituted with methylor phenyl fluorenyl group, or spirobifluorenyl group.

Also, Ar¹ and Ar² may be optionally substituted with one or moresubstituents selected from the group consisting of deuterium, halogen, asilane group, a siloxane group, a boron group, a germanium group, acyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxygroup, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynylgroup, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted withdeuterium, a fluorenyl group, a C₃-C₂₀ cycloalkyl group, a C₇-C₂₀arylalkyl group, and a C₈-C₂₀ arylalkenyl group.

In formula 1 above, L may be selected from the group consisting of aC₆-C₆₀ arylene group, a fluorenylene group, a fused ring group of aC₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring, a C₂-C₆₀ heterocyclicgroup containing at least one heteroatom selected from the groupconsisting of O, N, S, Si, and P, and combinations thereof.

preferably, L may be selected from the group consisting of a C₆-C₁₃arylene group, a fluorenylene group, or a C₃-C₁₂ heterocyclic group,also preferably, a C₆ arylene group, or C₄, C₅ heterocyclic group,specifically phenylene group, substituted or unsubstituted with methylfluorenylene group, pyridylene group or pyrimidinylene group.

Also preferably, L may be optionally substituted with one or moresubstituents selected from the group consisting of deuterium, halogen, asilane group, a siloxane group, a boron group, a germanium group, acyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxygroup, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynylgroup, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted bydeuterium, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P, a C₃-C₂₀ cycloalkyl group, a C₇-C₂₀ arylalkyl group, and a C₈-C₂₀arylalkenyl group.

In formula 1 above, R¹ to R⁴ may be each independently selected from thegroup consisting of hydrogen, deuterium, halogen, a C₆-C₆₀ aryl group, afluorenyl group, a C₂-C₆₀ heterocyclic group containing at least oneheteroatom selected from the group consisting of O, N, S, Si, and P, afused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring,C₁-C₅₀ alkyl group, C₂-C₂₀ alkenyl group, C₂-C₂₀ alkynyl group, C₁-C₃₀alkoxy group, C₆-C₃₀ aryloxy group, -L′-N(R^(a)) (R^(b)) andcombinations thereof. Each of m and n may be an integer of 0 to 4, eachof o and p may be an integer of 0 to 3. When m, n, o and p are each aninteger of 2 or more, each of plural R¹, R², R³ and R⁴ may be the sameor different.

Preferably, R¹ to R⁴ may be optionally substituted with one or moresubstituents selected from the group consisting of deuterium, halogen, asilane group, a siloxane group, a boron group, a germanium group, acyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxygroup, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynylgroup, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted withdeuterium, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing atleast one heteroatom selected from the group consisting of O, N, S, Si,and P, a C₃-C₂₀ cycloalkyl group, a C₇-C₂₀ arylalkyl group, and a C₈-C₂₀arylalkenyl group.

Also, any two adjacent groups of R^(1′) s to R^(4′)s may be optionallyformed ring, and R¹ to R⁴ don't form ring may be the same as definedabove. And the formed ring may be mono- or poly-cyclic ring.

L′ may be selected from the group consisting of a single bond, a C₆-C₆₀arylene group, a fluorenylene group, a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring, and a C₂-C₆₀ heterocyclicgroup containing at least one heteroatom selected from the groupconsisting of O, N, S, Si, and P.

R^(a) and R^(b) may be each independently selected from the groupconsisting of a C₆-C₆₀ aryl group, a fluorenyl group, a fused ring groupof a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring, and a C₂-C₆₀heterocyclic group containing at least one heteroatom selected from thegroup consisting of O, N, S, Si, and P.

Specifically, the compound of Formula 1 in the organic material layerabove may be represented by the following Formula 2 to Formula 5.

In Formula 2 to Formula 5, X, Y, Ar¹, Ar², L, R¹ to R⁴, m, n, o, p and qmay be the same as defined in Formula 1 above.

Specifically, the compound of Formula 1 in the organic material layerabove may be represented by the following Formula 6 and Formula 7.Formula 6 is represented when q is 1, Formula 7 is represented when q is2. In the formula 7, Ar¹s may be the same or different, and Ar²s may bethe same or different.

Wherein, X, Y, Ar¹, Ar², L, R¹ to R⁴, m, n, o and p may be the same asdefined in Formula 1.

More specifically, the compound of Formula 1 in the organic materiallayer above may be represented by one of the following compounds.

In another aspect of the present invention, there is provided an organicelectric element comprising an organic material layer comprising atleast one layer of a hole injection layer, a hole transport layer, or alight emitting layer comprising the compound represented by Formula 1.

Specifically, there is provided an organic electric element comprisingthe organic material layer comprising the compound represented byFormula 2 to Formula 7.

Specifically, there is provided an organic electric element comprisingthe organic material layer comprising one of the individual compounds.

Specifically, the compounds contained in the organic material layer maybe the same kind or two or more different kind of compounds representedby Formula 1. For example, the hole transport layer above may becomprised by single compound 1-1, or comprised by a mixture of thecompounds 1-1 and 1-2. Also, the emission auxiliary layer above may becomprised by single compound 1-1, or by a mixture of the compounds 1-1and 1-2.

Meanwhile, the organic material layer above may be formed by any one ofthe process of spin coating, nozzle printing, inkjet printing, slotcoating, dip coating and roll-to-roll.

In another aspect of the present invention, there is provided theorganic electric element further including at least one layer to improveluminous efficiency which is formed on at least one of the sides thefirst and second electrodes, which is opposite to the organic materiallayer. Specifically, the layer to improve luminous efficiency above maycomprise the compound represented by the Formula 1.

In another aspect of the present invention, there is provided anelectronic device comprising a display device which comprises theorganic electric element including the organic material layer containingthe compound according to the invention, and a control unit for drivingthe display device. Here, the organic electric element may be one of anorganic light emitting diode, an organic solar cell, an organic photoconductor, an organic transistor, and an element for monochromatic orwhite illumination.

Hereinafter, Synthesis Examples of the compounds represented by Formula1 according to the present invention and Preparation Examples of anorganic electric element will be described in detail by way of example.However, the following examples are only for illustrative purposes andare not intended to limit the scope of the invention.

SYNTHESIS EXAMPLE I. Synthesis Example of Formula 1

The final product of the present invention represented by Formula 1 canbe synthesized by reaction of Sub 1 and Sub 2 as illustrated in, but notlimited to, the following Reaction Scheme 1.

I. Synthesis Example of Sub 1

Sub 1 of the Reaction Scheme 1 can be synthesized according to, but notlimited to, the following Reaction Scheme 2.

(1) Synthesis Method of Sub 1-3(1)

A mixture of Sub 1-1(1) (4.6 g, 20 mmol), Sub 1-2(1) (6.3 g, 20 mmol),Pd(PPh₃)₄ (0.07 g, 0.06 mmol), K₂CO₃ (8.3 g, 60 mmol) was dissolved inanhydrous THF and trace amount of water, and refluxed for 24 hr. Aftercompletion of the reaction, temperature of the reaction solution wascooled to room temperature, extracted with CH₂Cl₂ and washed with water,dried over MgSO₄, and filtered concentrated in vacuo. The crude productwas purified by column chromatography to give Sub 1-3(1) (6.7 g, 80%).

(2) Synthesis Method of Sub 1-5(1)

A mixture of Sub 1-3(1) (6.7 g, 16 mmol), Sub 1-4(1) (3.6 g, 16 mmol),Pd(PPh₃)₄ (0.06 g, 0.05 mmol), K₂CO₃ (6.6 g, 48 mmol) was dissolved inanhydrous THF and trace amount of water, and refluxed for 24. Aftercompletion of the reaction, temperature of the reaction solution wascooled to room temperature, extracted with CH₂Cl₂, washed with water,dried over anhydrous MgSO₄, filtered and concentrated in vacuo. Thecrude product was purified by column chromatography to give Sub 1-5(1)(6.5 g, 78%).

(3) Synthesis Method of Sub 1(1)

To a solution of Sub 1-5(1) (6.5 g, 12.5 mmol) in DMF was addedBis(pinacolato)diboron (3.5 g, 13.8 mmol), PdCl₂(dppf) (0.3 g, 0.4mmol), KOAc (10.2 g, 36 mmol) and stirred at 90° C. After completion ofthe reaction, DMF was removed by distillation and extracted with CH₂Cl₂and water. Organic phases was dried over MgSO₄, concentrated in vacuo.The crude product was purified silicagel column and recrystallization togive Sub 1(1) (5.3 g, 75%).

2. Synthesis Method of 1(2)

(1) Synthesis Method of Sub 1-3(2)

Sub 1-1(2) (4.2 g, 20 mmol), Sub 1-2(1) (6.3 g, 20 mmol), Pd(PPh₃)₄(0.07 g, 0.06 mmol), K₂CO₃ (8.3 g, 60 mmol) was dissolved in anhydrousTHF and trace amount of water, and then Sub 1-3(2) (6.5 g, 81%) wasprepared according to the same way for Sub 1-3(1) above.

(2) Synthesis Method of Sub 1-5(2)

Sub 1-3(2) (6.5 g, 16 mmol), Sub 1-4(2) (3.4 g, 16 mmol), Pd(PPh₃)₄(0.06 g, 0.05 mmol), K₂CO₃ (6.6 g, 48 mmol) was dissolved in anhydrousTHF and trace amount of water, and then Sub 1-5(2) (6.2 g, 78%) wasprepared according to the same way for Sub 1-5(1) above.

(3) Synthesis Method of Sub 1(2)

To a solution of Sub 1-5(2) (6.1 g, 12.5 mmol) in DMF was addedBis(pinacolato)diboron (3.5 g, 13.8 mmol), PdCl₂(dppf) (0.3 g, 0.4mmol), KOAc (10.2 g, 36 mmol), and then Sub 1(2) (5.4 g, 80 was preparedaccording to the same way for Sub 1(1) above.

3. Synthesis Method of Sub 1(3)

(1) Synthesis Method of Sub 1-3(3)

Sub 1-1(3) (4.2 g, 20 mmol), Sub 1-2(1) (6.3 g, 20 mmol), Pd(PPh₃)₄(0.07 g, 0.06 mmol), K₂CO₃ (8.3 g, 60 mmol) was dissolved in anhydrousTHF and trace amount of water, and then Sub 1-3(3) (6.4 g, 79%) wasprepared according to the same way for Sub 1-3(1) above.

(2) Synthesis Method of Sub 1-5(3)

Sub 1-3(3) (6.5 g, 16 mmol), Sub 1-4(2) (3.7 g, 16 mmol), Pd(PPh₃)₄(0.06 g, 0.05 mmol), K₂CO₃ (6.6 g, 48 mmol) was dissolved in inanhydrous THF and trace amount of water, and then Sub 1-5(3) (6.5 g,80%) was prepared according to the same way for Sub 1-5(1).

(3) Synthesis Method of Sub 1(3)

To a solution of Sub 1-5(3) (6.3 g, 12.5 mmol) in DMF was addedBis(pinacolato)diboron (3.5 g, 13.8 mmol), PdCl₂(dppf) (0.3 g, 0.4mmol), KOAc (10.2 g, 36 mmol), and then Sub 1(3) (5.7 g, 82%) wasprepared according to the same way for Sub 1(1).

Examples of Sub 1 compounds include, but are not limited to, thefollowing compounds, and FD-MS (Field Desorption-Mass Spectrometry) dataof the compounds are given in Table 1 below.

TABLE 1 compounds FD-MS compounds FD-MS Sub 1(1) m/z =568.17(C₃₆H₂₉BO₂S₂ = 568.56) Sub 1(2) m/z = 536.22(C₃₆H₂₉BO₄ = 536.42)Sub 1(3) m/z = 552.19(C₃₆H₂₉BO₃S = 552.49) Sub 1(4) m/z =568.17(C₃₆H₂₉BO₂S₂ = 568.56) Sub 1(5) m/z = 568.17(C₃₆H₂₉BO₂S₂ = 568.56)Sub 1(6) m/z = 536.22(C₃₆H₂₉BO₄ = 536.42) Sub 1(7) m/z =536.22(C₃₆H₂₉BO₄ = 536.42) Sub 1(8) m/z = 536.22(C₃₆H₂₉BO₄ = 536.42) Sub1(9) m/z = 552.19(C₃₆H₂₉BO₃S = 552.49) Sub 1(10) m/z = 552.19(C₃₆H₂₉BO₃S= 552.49) Sub 1(11) m/z = 552.19(C₃₆H₂₉BO₃S = 552.49) Sub 1(12) m/z =568.17(C₃₆H₂₉BO₂S₂ = 568.56) Sub 1(13) m/z = 636.25(C₄₄H₃₃BO₄ = 636.54)Sub 1(14) m/z = 652.22(C₄₄H₃₃BO₃S = 652.61) Sub 1(15) m/z =768.23(C₅₂H₃₇BO₂S₂ = 768.79) Sub 1(16) m/z = 668.20(C₄₄H₃₃BO₂S₂ =668.67) Sub 1(17) m/z = 668.20(C₄₄H₃₃BO₂S₂ = 668.67) Sub 1(18) m/z =738.28(C₅₂H₃₇BO₄ = 736.66) Sub 1(19) m/z = 636.25(C₄₄H₃₃BO₄ = 636.54)

II. Synthesis Method of Sub 2

Sub 2 of the Reaction Scheme 1 can be synthesized according to, but notlimited to, the following Reaction Scheme 3.

(When q is 2, and when two of Ar¹ and two of Ar² are different, 2equivalents of Sub 2-3 can be substituted to 1 equivalent of Sub 2-4.)

1. Synthesis Method of Sub 2-(1)

(1) Synthesis Method of Sub 2-3(1)

To a solution of Sub 2-1(1) (1.9 g, 20 mmol), Sub 2-2(1) (3.5 g, 22mmol) in toluene was added Pd₂(dba)₃ (1.0 g, 1.1 mmol), PPh₃ (0.6 g, 2.2mmol), NaOt-Bu (6.3 g, 66 mmol), and refluxed at 100° C. for 24 hr. Andthen the solution was extracted with ether and water, dried over MgSO₄,evaporated in vacuo. The crude product was purified by silicagel columnand recrystallization to give Sub 2-3(1) (2.9 g, 85%)

(2) Synthesis Method of Sub 2-(1)

To a solution of Sub 2-3(1) (2.9 g, 17 mmol), Sub 2-4(1) (5.4 g, 19mmol) in toluene was added Pd₂(dba)₃ (0.9 g, 1 mmol), PPh₃ (0.5 g, 1.9mmol), NaOt-Bu (5.4 g, 57 mmol), and refluxed at 100° C. for 24 hr. Andthen the solution was extracted with ether and water, dried over MgSO₄,evaporated in vacuo. The crude product was purified by silicagel columnand recrystallization to give Sub 2-(1) (4.5 g, 81%)

2. Synthesis Method of Sub 2-(53)

(1) Synthesis Method of Sub 2-3(2)

To a solution of Sub 2-1(2) (3.4 g, 20 mmol), Sub 2-2(2) (5.1 g, 22mmol) in toluene was added Pd₂(dba)₃ (1.0 g, 1.1 mmol), PPh₃ (0.6 g, 2.2mmol), NaOt-Bu (6.3 g, 66 mmol), Sub 2-3(2) (5.0 g, 78%) was preparedaccording to the same way for Sub 2-3(1).

(2) Synthesis Method of Sub 2-(53)

To a solution of Sub 2-3(2) (5.0 g, 16 mmol), Sub 2-4(2) (9.0 g, 22mmol) in toluene was added Pd₂(dba)₃ (0.9 g, 1 mmol), PPh₃ (0.5 g, 1.9mmol), NaOt-Bu (5.4 g, 57 mmol), Sub 2-(53) (9.9 g, 80%) was preparedaccording to the same way for Sub 2-3(1).

Examples of Sub 2 compounds include, but are not limited to, thefollowing compounds, and FD-MS data of the compounds are given in Table2 below.

TABLE 2 compounds FD-MS compounds FD-MS Sub 2-(1) m/z = 323.03(C₁₈H₁₄BrN= 324.21) Sub 2-(2) m/z = 373.05(C₂₂H₁₆BrN = 374.27) Sub 2-(3) m/z =373.05(C₂₂H₁₆BrN = 374.27) Sub 2-(4) m/z = 399.06(C₂₄H₁₈BrN = 400.31)Sub 2-(5) m/z = 439.09(C₂₇H₂₂BrN = 440.37) Sub 2-(6) m/z =563.12(C₃₇H₂₆BrN = 564.51) Sub 2-(7) m/z = 561.11(C₃₇H₂₄BrN = 562.50)Sub 2-(8) m/z = 423.06(C₂₆H₁₈BrN = 424.33) Sub 2-(9) m/z =423.06(C₂₆H₁₈BrN = 424.33) Sub 2-(10) m/z = 449.08(C₂₈H₂₀BrN = 450.37)Sub 2-(11) m/z = 489.11(C₃₁H₂₄BrN = 490.43) Sub 2-(12) m/z =613.14(C₄₁H₂₈BrN = 641.57) Sub 2-(13) m/z = 611.12(C₄₁H₂₆BrN = 612.56)Sub 2-(14) m/z = 423.06(C₂₆H₁₈BrN = 424.33) Sub 2-(15) m/z =449.08(C₂₈H₂₀BrN = 450.37) Sub 2-(16) m/z = 489.11(C₃₁H₂₄BrN = 490.43)Sub 2-(17) m/z = 613.14(C₄₁H₂₈BrN = 614.57) Sub 2-(18) m/z =611.12(C₄₁H₂₆BrN = 612.56) Sub 2-(19) m/z = 475.09(C₃₀H₂₂BrN = 476.41)Sub 2-(20) m/z = 515.12(C₃₃H₂₆BrN = 516.47) Sub 2-(21) m/z =639.16(C₄₃H₃₀BrN = 640.61) Sub 2-(22) m/z = 637.14(C₄₃H₂₈BrN = 638.59)Sub 2-(23) m/z = 399.06(C₂₄H₁₈BrN = 400.31) Sub 2-(24) m/z =449.08(C₂₈H₂₀BrN = 450.37) Sub 2-(25) m/z = 449.08(C₂₈H₂₀BrN = 450.37)Sub 2-(26) m/z = 475.09(C₃₀H₂₂BrN = 476.41) Sub 2-(27) m/z =515.12(C₃₃H₂₆BrN = 516.47) Sub 2-(28) m/z = 639.16(C₄₃H₃₀BrN = 640.61)Sub 2-(29) m/z = 637.14(C₄₃H₂₈BrN = 638.59) Sub 2-(30) m/z =499.09(C₃₂H₂₂BrN = 500.43) Sub 2-(31) m/z = 499.09(C₃₂H₂₂BrN = 500.43)Sub 2-(32) m/z = 525.11(C₃₄H₂₄BrN = 526.47) Sub 2-(33) m/z =565.14(C₃₇H₂₈BrN = 566.53) Sub 2-(34) m/z = 689.17(C₄₇H₃₂BrN = 690.67)Sub 2-(35) m/z = 687.16(C₄₇H₃₀BrN = 688.65) Sub 2-(36) m/z =499.09(C₃₂H₂₂BrN = 500.43) Sub 2-(37) m/z = 525.11(C₃₄H₂₄BrN = 526.47)Sub 2-(38) m/z = 565.14(C₃₇H₂₈BrN = 566.53) Sub 2-(39) m/z =689.17(C₄₇H₃₂BrN = 690.67) Sub 2-(40) m/z = 687.16(C₄₇H₃₀BrN = 688.65)Sub 2-(41) m/z = 551.12(C₃₆H₂₆BrN = 552.50) Sub 2-(42) m/z =591.16(C₃₉H₃₀BrN = 592.57) Sub 2-(43) m/z = 715.19(C₄₉H₃₄BrN = 716.70)Sub 2-(44) m/z = 713.17(C₄₉H₃₂BrN = 714.69) Sub 2-(45) m/z =475.09(C₃₀H₂₂BrN = 476.41) Sub 2-(46) m/z = 551.12(C₃₆H₂₆BrN = 552.50)Sub 2-(47) m/z = 591.16(C₃₉H₃₀BrN = 592.57) Sub 2-(48) m/z =715.19(C₄₉H₃₄BrN = 716.70) Sub 2-(49) m/z = 713.17(C₄₉H₃₂BrN = 714.69)Sub 2-(50) m/z = 490.10(C₃₀H₂₃BrN₂ = 491.42) Sub 2-(51) m/z =690.17(C₄₆H₃₁BrN₂ = 691.7) Sub 2-(52) m/z = 690.17(C₄₆H₃₁BrN₂ = 691.7)Sub 2-(53) m/z = 794.23(C₅₄H₃₉BrN₂ = 795.8) Sub 2-(54) m/z =489.11(C₃₁H₂₄BrN = 490.43) Sub 2-(55) m/z = 476.09(C₂₉H₂₁BrN₂ = 477.39)Sub 2-(56) m/z = 477.08(C₂₈H₂₀BrN₃ = 478.38)

III. Synthesis Method of Final Product

To a dissolving solution of Sub 1 (1 eq) in THF was added Sub 2 (1.2eq), Pd(PPh₃)₄ (0.035 eq), NaOH (3 eq), and water, and then refluxed.After completion of the reaction, the reaction solution was extractedwith ether and water, and dried over MgSO₄ and evaporated. The crudeproduct was purified by silicagel column and recrystallization to give aFinal Product.

1. Synthesis Method of 1-25

To a dissolving solution of Sub 1(1) (11.4 g, 20 mmol) in THF was addedSub 2-(19) (11.4 g, 24 mmol), Pd(PPh₃)₄ (0.8 g, 0.7 mmol), NaOH (2.4 g,60 mmol), and water, and then refluxed. After completion of thereaction, the reaction solution was extracted with ether and water, anddried over MgSO₄ and evaporated. The crude product was purified bysilicagel column and recrystallization to give 1-25 (14.1 g, 84%).

2. Synthesis Method of 2-26

To a dissolving solution of Sub 1(6) (10.7 g, 20 mmol) in THF was addedSub 2-(20) (12.4 g, 24 mmol), Pd(PPh₃)₄ (0.8 g, 0.7 mmol), NaOH (2.4 g,60 mmol), and water. And then 2-26(13.2 g, 78%) was prepared accordingto the same way for 1-25.

3. Synthesis Method of 4-35

To a dissolving solution of Sub 1(2) (10.7 g, 20 mmol) in THF was addedSub 2-(56) (11.5 g, 24 mmol), Pd(PPh₃)₄ (0.8 g, 0.7 mmol), NaOH (2.4 g,60 mmol), and water. And then 4-35 (12.1 g, 75%) was prepared accordingto the same way for 1-25.

4. Synthesis Method of 6-1

To a dissolving solution of Sub 1(10) (11.0 g, 20 mmol) in THF was addedSub 2-(1) (7.8 g, 24 mmol), Pd(PPh₃)₄ (0.8 g, 0.7 mmol), NaOH (2.4 g, 60mmol), and water. And then 6-1 (12.1 g, 75%) was prepared according tothe same way for 1-25.

5. Synthesis Method of 7-1

To a dissolving solution of Sub 1(5) (11.4 g, 20 mmol) in THF was addedSub 2-(1) (7.8 g, 24 mmol), Pd(PPh₃)₄ (0.8 g, 0.7 mmol), NaOH (2.4 g, 60mmol), and water. And then 7-1 (11.0 g, 80%) was prepared according tothe same way for 1-25.

6. Synthesis Method of 7-9

To a dissolving solution of Sub 1(1) (11.4 g, 20 mmol) in THF was addedSub 2-(50) (11.8 g, 24 mmol), Pd(PPh₃)₄ (0.8 g, 0.7 mmol), NaOH (2.4 g,60 mmol), and water. And then 7-9 (12.6 g, 74%) was prepared accordingto the same way for 1-25.

TABLE 3 compounds FD-MS compounds FD-MS 1-1 m/z = 685.19(C₄₈H₃₁NS₂ =685.90) 1-2 m/z = 735.21(C₅₂H₃₃NS₂ = 735.96) 1-3 m/z = 735.21(C₅₂H₃₃NS₂= 735.96) 1-4 m/z = 761.22(C₅₄H₃₅NS₂ = 761.99) 1-5 m/z =801.25(C₅₇H₃₉NS₂ = 802.06) 1-6 m/z = 925.28(C₆₇H₄₃NS₂ = 926.20) 1-7 m/z= 923.27(C₆₇H₄₁NS₂ = 924.18) 1-8 m/z = 785.22(C₅₆H₃₅NS₂ = 786.01) 1-9m/z = 785.22(C₅₆H₃₅NS₂ = 786.01) 1-10 m/z = 811.24(C₅₈H₃₇NS₂ = 812.05)1-11 m/z = 851.27(C₆₁H₄₁NS₂ = 852.11) 1-12 m/z = 975.30(C₇₁H₄₅NS₂ =976.25) 1-13 m/z = 973.28(C₇₁H₄₃NS₂ = 974.24) 1-14 m/z =785.22(C₅₆H₃₅NS₂ = 786.01) 1-15 m/z = 811.24(C₅₈H₃₇NS₂ = 812.05) 1-16m/z = 851.27(C₆₁H₄₁NS₂ = 852.11) 1-17 m/z = 975.30(C₇₁H₄₅NS₂ = 976.25)1-18 m/z = 973.28(C₇₁H₄₃NS₂ = 974.24) 1-19 m/z = 837.25(C₆₀H₃₉NS₂ =838.09) 1-20 m/z = 877.28(C₆₃H₄₃NS₂ = 878.15) 1-21 m/z =1001.31(C₇₃H₄₇NS₂ = 1002.29) 1-22 m/z = 999.30(C₇₃H₄₅NS₂ = 1000.28) 1-23m/z = 837.25(C₆₀H₃₉NS₂ = 838.09) 1-24 m/z = 937.28(C₆₈H₄₃NS₂ = 938.21)1-25 m/z = 937.28(C₆₈H₄₃NS₂ = 938.21) 1-26 m/z = 838.25(C₅₉H₃₈N₂S₂ =839.08) 1-27 m/z = 839.24(C₅₈H₃₇N₃S₂ = 840.06) 1-28 m/z =913.28(C₆₆H₄₃NS₂ = 914.18) 2-1 m/z = 653.24(C₄₈H₃₁NO₂ = 653.77) 2-2 m/z= 703.25(C₅₂H₃₃NO₂ = 703.82) 2-3 m/z = 703.25(C₅₂H₃₃NO₂ = 703.82) 2-4m/z = 729.27(C₅₄H₃₅NO₂ = 729.86) 2-5 m/z = 769.30(C₅₇H₃₉NO₂ = 769.93)2-6 m/z = 893.33(C₆₇H₄₃NO₂ = 894.06) 2-7 m/z = 891.31(C₆₇H₄₁NO₂ =892.05) 2-8 m/z = 753.27(C₅₆H₃₅NO₂ = 753.88) 2-9 m/z = 753.27(C₅₆H₃₅NO₂= 753.88) 2-10 m/z = 779.28(C₅₈H₃₇NO₂ = 779.92) 2-11 m/z =819.31(C₆₁H₄₁NO₂ = 819.98) 2-12 m/z = 943.35(C₇₁H₄₅NO₂ = 944.12) 2-13m/z = 941.33(C₇₁H₄₃NO₂ = 942.11) 2-14 m/z = 753.27(C₅₆H₃₅NO₂ = 753.88)2-15 m/z = 779.28(C₅₈H₃₇NO₂ = 779.92) 2-16 m/z = 819.31(C₆₁H₄₁NO₂ =819.98) 2-17 m/z = 943.35(C₇₁H₄₅NO₂ = 944.12) 2-18 m/z =941.33(C₇₁H₄₃NO₂ = 942.11) 2-19 m/z = 805.30(C₆₀H₃₉NO₂ = 805.96) 2-20m/z = 845.33(C₆₃H₄₃NO₂ = 846.02) 2-21 m/z = 969.36(C₇₃H₄₇NO₂ = 970.16)2-22 m/z = 967.35(C₇₃H₄₅NO₂ = 968.14) 2-23 m/z = 805.30(C₆₀H₃₉NO₂ =805.96) 2-24 m/z = 905.33(C₆₈H₄₃NO₂ = 906.07) 2-25 m/z =905.33(C₆₈H₄₃NO₂ = 906.07) 2-26 m/z = 806.29(C₅₉H₃₈N₂O₂ = 806.95) 2-27m/z = 807.29(C₅₈H₃₇N₃O₂ = 807.93) 2-28 m/z = 881.33(C₆₆H₄₃NO₂ = 882.05)3-1 m/z = 685.19(C₄₈H₃₁NS₂ = 685.90) 3-2 m/z = 735.21(C₅₂H₃₃NS₂ =735.96) 3-3 m/z = 735.21(C₅₂H₃₃NS₂ = 735.96) 3-4 m/z = 761.22(C₅₄H₃₅NS₂= 761.99) 3-5 m/z = 801.25(C₅₇H₃₉NS₂ = 802.06) 3-6 m/z =925.28(C₆₇H₄₃NS₂ = 926.20) 3-7 m/z = 923.27(C₆₇H₄₁NS₂ = 924.18) 3-8 m/z= 785.22(C₅₆H₃₅NS₂ = 786.01) 3-9 m/z = 785.22(C₅₆H₃₅NS₂ = 786.01) 3-10m/z = 811.24(C₅₈H₃₇NS₂ = 812.05) 3-11 m/z = 851.27(C₆₁H₄₁NS₂ = 852.11)3-12 m/z = 975.30(C₇₁H₄₅NS₂ = 976.25) 3-13 m/z = 973.28(C₇₁H₄₃NS₂ =974.24) 3-14 m/z = 785.22(C₅₆H₃₅NS₂ = 786.01) 3-15 m/z =811.24(C₅₈H₃₇NS₂ = 812.05) 3-16 m/z = 851.27(C₆₁H₄₁NS₂ = 852.11) 3-17m/z = 975.30(C₇₁H₄₅NS₂ = 976.25) 3-18 m/z = 973.28(C₇₁H₄₃NS₂ = 974.24)3-19 m/z = 837.25(C₆₀H₃₉NS₂ = 838.09) 3-20 m/z = 877.28(C₆₃H₄₃NS₂ =878.15) 3-21 m/z = 1001.31(C₇₃H₄₇NS₂ = 1002.29) 3-22 m/z =999.30(C₇₃H₄₅NS₂ = 1000.28) 3-23 m/z = 837.25(C₆₀H₃₉NS₂ = 838.09) 3-24m/z = 937.28(C₆₈H₄₃NS₂ = 938.21) 3-25 m/z = 937.28(C₆₈H₄₃NS₂ = 938.21)3-26 m/z = 838.25(C₅₉H₃₈N₂S₂ = 839.08) 3-27 m/z = 839.24(C₅₈H₃₇N₃S₂ =840.06) 3-28 m/z = 913.28(C₆₆H₄₃NS₂ = 914.18) 4-1 m/z = 653.24(C₄₈H₃₁NO₂= 653.77) 4-2 m/z = 703.25(C₅₂H₃₃NO₂ = 703.82) 4-3 m/z =703.25(C₅₂H₃₃NO₂ = 703.82) 4-4 m/z = 729.27(C₅₄H₃₅NO₂ = 729.86) 4-5 m/z= 769.30(C₅₇H₃₉NO₂ = 769.93) 4-6 m/z = 893.33(C₆₇H₄₃NO₂ = 894.06) 4-7m/z = 891.31(C₆₇H₄₁NO₂ = 892.05) 4-8 m/z = 753.27(C₅₆H₃₅NO₂ = 753.88)4-9 m/z = 753.27(C₅₆H₃₅NO₂ = 753.88) 4-10 m/z = 779.28(C₅₈H₃₇NO₂ =779.92) 4-11 m/z = 819.31(C₆₁H₄₁NO₂ = 819.98) 4-12 m/z =943.35(C₇₁H₄₅NO₂ = 944.12) 4-13 m/z = 941.33(C₇₁H₄₃NO₂ = 942.11) 4-14m/z = 753.27(C₅₆H₃₅NO₂ = 753.88) 4-15 m/z = 779.28(C₅₈H₃₇NO₂ = 779.92)4-16 m/z = 819.31(C₆₁H₄₁NO₂ = 819.98) 4-17 m/z = 943.35(C₇₁H₄₅NO₂ =944.12) 4-18 m/z = 941.33(C₇₁H₄₃NO₂ = 942.11) 4-19 m/z =805.30(C₆₀H₃₉NO₂ = 805.96) 4-20 m/z = 845.33(C₆₃H₄₃NO₂ = 846.02) 4-21m/z = 969.36(C₇₃H₄₇NO₂ = 970.16) 4-22 m/z = 967.35(C₇₃H₄₅NO₂ = 968.14)4-23 m/z = 805.30(C₆₀H₃₉NO₂ = 805.96) 4-24 m/z = 905.33(C₆₈H₄₃NO₂ =906.07) 4-25 m/z = 905.33(C₆₈H₄₃NO₂ = 906.07) 4-26 m/z =806.29(C₅₉H₃₈N₂O₂ = 806.95) 4-27 m/z = 807.29(C₅₈H₃₇N₃O₂ = 807.93) 4-28m/z = 881.33(C₆₆H₄₃NO₂ = 882.05) 5-1 m/z = 937.28(C₆₈H₄₃NS₂ = 938.21)5-3 m/z = 905.33(C₆₈H₄₃NO₂ = 906.07) 5-2 m/z = 937.28(C₆₈H₄₃NS₂ =938.21) 5-4 m/z = 1005.36(C₇₆H₄₇NO₂ = 1006.19) 6-1 m/z =669.21(C₄₈H₃₁NOS = 669.83) 6-2 m/z = 719.23(C₅₂H₃₃NOS = 719.89) 6-3 m/z= 719.23(C₅₂H₃₃NOS = 719.89) 6-4 m/z = 745.24(C₅₄H₃₅NOS = 745.93) 6-5m/z = 785.28(C₅₇H₃₉NOS = 785.99) 6-6 m/z = 909.31(C₆₇H₄₃NOS = 910.13)6-7 m/z = 907.29(C₆₇H₄₁NOS = 908.11) 6-8 m/z = 769.24(C₅₆H₃₅NOS =769.95) 6-9 m/z = 769.24(C₅₆H₃₅NOS = 769.95) 6-10 m/z = 795.26(C₅₈H₃₇NOS= 795.99) 6-11 m/z = 835.29(C₆₁H₄₁NOS = 836.05) 6-12 m/z =959.32(C₇₁H₄₅NOS = 960.19) 6-13 m/z = 957.31(C₇₁H₄₃NOS = 958.17) 6-14m/z = 769.24(C₅₆H₃₅NOS = 769.95) 6-15 m/z = 795.26(C₅₈H₃₇NOS = 795.99)6-16 m/z = 835.29(C₆₁H₄₁NOS = 836.05) 6-17 m/z = 959.32(C₇₁H₄₅NOS =960.19) 6-18 m/z = 957.31(C₇₁H₄₃NOS = 958.17) 6-19 m/z =821.28(C₆₀H₃₉NOS = 822.02) 6-20 m/z = 861.31(C₆₃H₄₃NOS = 862.09) 6-21m/z = 985.34(C₇₃H₄₇NOS = 986.23) 6-22 m/z = 983.32(C₇₃H₄₅NOS = 984.21)6-23 m/z = 821.28(C₆₀H₃₉NOS = 822.02) 6-24 m/z = 921.31(C₆₈H₄₃NOS =922.14) 6-25 m/z = 921.31(C₆₈H₄₃NOS = 922.14) 6-26 m/z =822.27(C₅₉H₃₈N₂OS = 823.01) 6-27 m/z = 823.27(C₅₈H₃₇N₃OS = 824.00) 6-28m/z = 897.31(C₆₆H₄₃NOS = 898.12) 7-1 m/z = 685.19(C₄₈H₃₁NS₂ = 685.90)7-2 m/z = 735.21(C₅₂H₃₃NS₂ = 735.96) 7-3 m/z = 735.21(C₅₂H₃₃NS₂ =735.96) 7-4 m/z = 761.22(C₅₄H₃₅NS₂ = 761.99) 7-5 m/z = 769.30(C₅₇H₃₉NO₂= 769.93) 7-6 m/z = 893.33(C₆₇H₄₃NO₂ = 894.06) 7-7 m/z =907.29(C₆₇H₄₁NOS = 908.11) 7-8 m/z = 469.24(C₅₆H₃₅NOS = 769.95) 7-9 m/z= 852.26(C₆₀H₄₀N₂S₂ = 853.10) 7-10 m/z = 1052.33(C₇₆H₄₈N₂S₂ = 1053.34)7-11 m/z = 1052.33(C₇₆H₄₈N₂S₂ = 1053.34) 7-12 m/z = 1156.39(C₈₄H₅₆N₂S₂ =1157.49) 7-13 m/z = 820.31(C₆₀H₄₀N₂O₂ = 820.97) 7-14 m/z =1020.37(C₇₆H₄₈N₂O₂ = 1021.21) 7-15 m/z = 1020.37(C₇₆H₄₈N₂O₂ = 1021.21)7-16 m/z = 1124.43(C₈₄H₅₆N₂O₂ = 1125.36) 7-17 m/z = 836.29(C₆₀H₄₀N₂OS =837.04) 7-18 m/z = 1036.35(C₇₆H₄₈N₂OS = 1037.27) 7-19 m/z =1036.35(C₇₆H₄₈N₂OS = 1037.27) 7-20 m/z = 1140.41(C₈₄H₅₆N₂OS = 1141.42)7-21 m/z = 1268.42(C₉₃H₆₀N₂S₂ = 1269.61) 7-22 m/z = 1166.37(C₈₅H₅₄N₂S₂ =1167.48) 7-23 m/z = 1140.41(C₈₄H₅₆N₂OS = 1141.42) 7-24 m/z =1324.50(C₁₀₀H₆₄N₂O₂ = 1325.6)

Fabrication and Evaluation of Organic Electronic Element Test Example 1Green Organic Light Emitting Diode (a Hole Transport Layer)

Organic light emitting diodes (OLEDs) were fabricated according to aconventional method by using a synthesized compound as a hole transportlayer material. First, an ITO layer (anode) was formed on a glasssubstrate, and a film ofN¹-(naphthalen-2-yl)N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine(hereinafter, “2-TNATA”) was vacuum-deposited on the ITO layer to form ahole injection layer with a thickness of 60 nm. Subsequently, a film ofthe compound 1-1 of the present invention was vacuum-deposited on thehole injection layer to form a hole transport layer with a thickness of60 nm. Subsequently, a light emitting layer with a thickness of 30 nmwas deposited on the hole transport layer by doping the hole transportlayer with the 4,4′-N,N′-dicarbazole-biphenyl (hereinafter, “CBP”) as ahost material and tris(2-phenylpyridine)-iridium (hereinafter,“Ir(ppy)₃”) as a dopant material in a weight ratio of 90:10. Next, afilm of ((1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter, “BAlq”) was vacuum-deposited with a thickness of 10 nm onthe light emitting layer to form a hole blocking layer, and a film oftris(8-quinolinolato)aluminum (hereinafter, “Alq₃”) was formed with athickness of 40 nm to form an electron transport layer. Next, LiF ashalogenated alkali metal was deposited with a thickness of 0.2 nm on theelectron transport layer to form an electron injection layer, and thenAl was deposited with a thickness of 150 nm on the electron injectionlayer to form a cathode. In this way, the OLED was completed.

[Test Example 2] to [Test Example 138] Green Organic Light EmittingDiode (a Hole Transport Layer)

The OLED was manufactured in the same manner as described in TestExample 1, except that any one of the compounds 1-2 to 1-28, 2-1 to2-28, 3-1 to 3-28, 4-1 to 4-28, 5-1, 5-2, 6-19 to 6-23, and 7-1 to 7-20of the present invention in the Table 4 below was used as the holetransport layer material, instead of the inventive compound 1-1.

Comparative Example 1 Green Organic Light Emitting Diode (a HoleTransport Layer)

An OLED was manufactured in the same manner as described in Test Example1, except that Comparative Compound A represented below was used as thehole transport layer material, instead of the inventive compound 1-1.

Comparative Compound A

Comparative Example 2 Green Organic Light Emitting Diode (a HoleTransport Layer)

An OLED was manufactured in the same manner as described in Test Example1, except that Comparative Compound B represented below was used as thehole transport layer material, instead of the inventive compound 1-1.

Comparative Compound B

Comparative Example 3 Green Organic Light Emitting Diode (a HoleTransport Layer)

An OLED was manufactured in the same manner as described in Test Example1, except that Comparative Compound C represented below was used as thehole transport layer material, instead of the inventive compound 1-1.

Comparative Compound C

Comparative Example 4 Green Organic Light Emitting Diode (a HoleTransport Layer)

An OLED was manufactured in the same manner as described in Test Example1, except that Comparative Compound D represented below was used as thehole transport layer material, instead of the inventive compound 1-1.

Comparative Compound D

A forward bias DC voltage was applied to each of the OLEDs manufacturedthrough Test Examples 1 to 138 and Comparative Example 1 to 4, andelectro-luminescence (EL) characteristics of the OLED were measured byPR-650 (Photoresearch). Also, T95 life span was measured by life spanmeasuring equipment (Mcscience) at a reference brightness of 5000 cd/m².Table 4 below shows evaluation results of OLEDs manufactured TestExamples and Comparative Examples.

TABLE 4 Current Voltage Density Brightness Efficiency Lifetime CIECompound (V) (mA/cm²) (cd/m²) (cd/A) T(95) (x, y) Com. Ex(1) Com. Com. A6.4 20.8 5000.0 24.0 60.2 (0.31, 0.60) Com. Ex(2) Com. Com. B 6.0 14.85000.0 33.8 78.3 (0.31, 0.61) Com. Ex(3) Com. Com. C 6.2 16.5 5000.030.2 72.5 (0.31, 0.60) Com. Ex(4) Com. Com. D 6.1 18.0 5000.0 27.8 75.5(0.33, 0.61) Ex.(1) Com.(1-1) 5.1 9.8 5000.0 50.9 94.3 (0.30, 0.60)Ex.(2) Com.(1-2) 5.2 9.6 5000.0 52.1 105.5 (0.31, 0.61) Ex.(3) Com.(1-3)5.1 9.7 5000.0 51.3 123.5 (0.31, 0.60) Ex.(4) Com.(1-4) 5.1 9.5 5000.052.5 91.6 (0.33, 0.61) Ex.(5) Com.(1-5) 5.2 9.2 5000.0 54.6 114.7 (0.32,0.61) Ex.(6) Com.(1-6) 5.1 9.9 5000.0 50.7 142.3 (0.33, 0.60) Ex.(7)Com.(1-7) 5.2 9.3 5000.0 54.0 131.4 (0.32, 0.61) Ex.(8) Com.(1-8) 5.210.0 5000.0 50.1 126.9 (0.31, 0.60) Ex.(9) Com.(1-9) 5.1 9.8 5000.0 51.094.1 (0.31, 0.61) Ex.(10) Com.(1-10) 5.1 9.3 5000.0 53.8 108.9 (0.31,0.60) Ex.(11) Com.(1-11) 5.1 9.4 5000.0 53.0 98.2 (0.33, 0.61) Ex.(12)Com.(1-12) 5.1 9.2 5000.0 54.6 111.1 (0.30, 0.60) Ex.(13) Com.(1-13) 5.29.7 5000.0 51.5 122.9 (0.31, 0.61) Ex.(14) Com.(1-14) 5.0 9.4 5000.053.3 106.5 (0.31, 0.60) Ex.(15) Com.(1-15) 5.1 9.7 5000.0 51.3 98.0(0.33, 0.61) Ex.(16) Com.(1-16) 5.1 10.0 5000.0 50.0 149.1 (0.32, 0.61)Ex.(17) Com.(1-17) 5.1 9.6 5000.0 52.2 145.2 (0.33, 0.60) Ex.(18)Com.(1-18) 5.1 10.0 5000.0 50.1 133.0 (0.32, 0.61) Ex.(19) Com.(1-19)5.1 9.3 5000.0 53.5 138.9 (0.31, 0.60) Ex.(20) Com.(1-20) 5.0 9.9 5000.050.5 110.3 (0.31, 0.61) Ex.(21) Com.(1-21) 5.2 9.3 5000.0 54.1 102.9(0.31, 0.60) Ex.(22) Com.(1-22) 5.1 9.2 5000.0 54.2 135.7 (0.33, 0.61)Ex.(23) Com.(1-23) 5.0 9.6 5000.0 52.3 120.5 (0.30, 0.60) Ex.(24)Com.(1-24) 5.0 9.7 5000.0 51.3 111.4 (0.31, 0.61) Ex.(25) Com.(1-25) 5.19.5 5000.0 52.8 115.7 (0.31, 0.60) Ex.(26) Com.(1-26) 5.1 9.8 5000.050.9 91.4 (0.33, 0.61) Ex.(27) Com.(1-27) 5.0 9.3 5000.0 54.0 127.4(0.32, 0.61) Ex.(28) Com.(1-28) 5.2 9.6 5000.0 52.2 128.1 (0.33, 0.60)Ex.(29) Com.(2-1) 5.5 11.2 5000.0 44.7 124.6 (0.31, 0.61) Ex.(30)Com.(2-2) 5.5 11.8 5000.0 42.5 122.1 (0.31, 0.60) Ex.(31) Com.(2-3) 5.511.5 5000.0 43.4 117.3 (0.33, 0.61) Ex.(32) Com.(2-4) 5.4 12.1 5000.041.4 113.0 (0.32, 0.61) Ex.(33) Com.(2-5) 5.4 11.3 5000.0 44.2 99.7(0.33, 0.60) Ex.(34) Com.(2-6) 5.4 11.6 5000.0 43.0 99.9 (0.32, 0.61)Ex.(35) Com.(2-7) 5.4 11.2 5000.0 44.6 123.8 (0.31, 0.60) Ex.(36)Com.(2-8) 5.4 11.4 5000.0 43.8 91.4 (0.31, 0.61) Ex.(37) Com.(2-9) 5.511.2 5000.0 44.5 132.4 (0.31, 0.60) Ex.(38) Com.(2-10) 5.4 11.7 5000.042.7 145.5 (0.33, 0.61) Ex.(39) Com.(2-11) 5.4 12.3 5000.0 40.5 115.0(0.30, 0.60) Ex.(40) Com.(2-12) 5.5 11.4 5000.0 43.9 121.0 (0.31, 0.61)Ex.(41) Com.(2-13) 5.4 12.3 5000.0 40.8 133.8 (0.31, 0.60) Ex.(42)Com.(2-14) 5.4 12.2 5000.0 41.1 128.7 (0.33, 0.61) Ex.(43) Com.(2-15)5.4 12.4 5000.0 40.2 130.8 (0.32, 0.61) Ex.(44) Com.(2-16) 5.5 12.05000.0 41.6 123.7 (0.33, 0.60) Ex.(45) Com.(2-17) 5.4 11.1 5000.0 44.8112.9 (0.32, 0.61) Ex.(46) Com.(2-18) 5.4 11.3 5000.0 44.3 105.1 (0.31,0.60) Ex.(47) Com.(2-19) 5.5 12.1 5000.0 41.2 132.8 (0.31, 0.61) Ex.(48)Com.(2-20) 5.4 12.4 5000.0 40.4 96.8 (0.31, 0.60) Ex.(49) Com.(2-21) 5.511.6 5000.0 43.0 103.8 (0.33, 0.61) Ex.(50) Com.(2-22) 5.5 11.7 5000.042.8 146.7 (0.30, 0.60) Ex.(51) Com.(2-23) 5.5 12.1 5000.0 41.5 147.5(0.31, 0.61) Ex.(52) Com.(2-24) 5.5 12.3 5000.0 40.7 130.1 (0.31, 0.60)Ex.(53) Com.(2-25) 5.5 11.8 5000.0 42.2 96.2 (0.33, 0.61) Ex.(54)Com.(2-26) 5.4 12.4 5000.0 40.4 122.0 (0.32, 0.61) Ex.(55) Com.(2-27)5.4 11.9 5000.0 42.0 106.4 (0.33, 0.60) Ex.(56) Com.(2-28) 5.5 11.25000.0 44.7 114.4 (0.32, 0.61) Ex.(57) Com.(3-1) 5.2 9.6 5000.0 52.2129.2 (0.31, 0.60) Ex.(58) Com.(3-2) 5.1 9.1 5000.0 54.8 145.3 (0.33,0.61) Ex.(59) Com.(3-3) 5.2 9.5 5000.0 52.6 148.5 (0.30, 0.60) Ex.(60)Com.(3-4) 5.1 9.7 5000.0 51.3 124.1 (0.31, 0.61) Ex.(61) Com.(3-5) 5.29.6 5000.0 51.8 125.6 (0.31, 0.60) Ex.(62) Com.(3-6) 5.1 10.0 5000.050.0 146.6 (0.33, 0.61) Ex.(63) Com.(3-7) 5.1 9.6 5000.0 52.1 103.9(0.32, 0.61) Ex.(64) Com.(3-8) 5.1 9.1 5000.0 54.8 104.9 (0.33, 0.60)Ex.(65) Com.(3-9) 5.1 9.8 5000.0 51.1 141.7 (0.32, 0.61) Ex.(66)Com.(3-10) 5.2 9.9 5000.0 50.7 92.1 (0.31, 0.60) Ex.(67) Com.(3-11) 5.19.1 5000.0 54.9 140.3 (0.31, 0.61) Ex.(68) Com.(3-12) 5.1 9.1 5000.054.8 131.6 (0.31, 0.60) Ex.(69) Com.(3-13) 5.0 9.5 5000.0 52.8 125.3(0.33, 0.61) Ex.(70) Com.(3-14) 5.1 9.9 5000.0 50.7 94.4 (0.30, 0.60)Ex.(71) Com.(3-15) 5.0 10.0 5000.0 50.2 130.3 (0.31, 0.61) Ex.(72)Com.(3-16) 5.1 9.8 5000.0 51.0 141.1 (0.31, 0.60) Ex.(73) Com.(3-17) 5.19.9 5000.0 50.4 113.6 (0.33, 0.61) Ex.(74) Com.(3-18) 5.2 9.5 5000.052.9 119.3 (0.32, 0.61) Ex.(75) Com.(3-19) 5.1 9.3 5000.0 53.5 133.7(0.33, 0.61) Ex.(76) Com.(3-20) 5.1 9.3 5000.0 53.5 112.3 (0.30, 0.60)Ex.(77) Com.(3-21) 5.1 9.5 5000.0 52.5 114.8 (0.31, 0.61) Ex.(78)Com.(3-22) 5.1 9.6 5000.0 51.8 92.2 (0.31, 0.60) Ex.(79) Com.(3-23) 5.19.6 5000.0 52.0 107.4 (0.33, 0.61) Ex.(80) Com.(3-24) 5.1 9.2 5000.054.4 127.4 (0.32, 0.61) Ex.(81) Com.(3-25) 5.1 9.6 5000.0 52.2 128.4(0.33, 0.60) Ex.(82) Com.(3-26) 5.1 9.1 5000.0 54.8 103.6 (0.32, 0.61)Ex.(83) Com.(3-27) 5.1 9.5 5000.0 52.6 102.9 (0.31, 0.60) Ex.(84)Com.(3-28) 5.0 9.7 5000.0 51.3 105.1 (0.31, 0.61) Ex.(85) Com.(4-1) 5.411.6 5000.0 43.2 141.1 (0.31, 0.60) Ex.(86) Com.(4-2) 5.4 11.4 5000.043.8 148.2 (0.33, 0.61) Ex.(87) Com.(4-3) 5.4 11.1 5000.0 44.9 121.6(0.30, 0.60) Ex.(88) Com.(4-4) 5.4 12.4 5000.0 40.2 138.3 (0.31, 0.61)Ex.(89) Com.(4-5) 5.4 11.5 5000.0 43.4 135.4 (0.31, 0.60) Ex.(90)Com.(4-6) 5.5 12.3 5000.0 40.6 143.5 (0.33, 0.61) Ex.(91) Com.(4-7) 5.411.5 5000.0 43.3 124.1 (0.32, 0.61) Ex.(92) Com.(4-8) 5.5 11.6 5000.043.2 107.6 (0.33, 0.60) Ex.(93) Com.(4-9) 5.5 11.2 5000.0 44.8 90.8(0.31, 0.61) Ex.(94) Com.(4-10) 5.5 12.1 5000.0 41.2 148.4 (0.31, 0.60)Ex.(95) Com.(4-11) 5.5 11.6 5000.0 43.2 105.3 (0.33, 0.61) Ex.(96)Com.(4-12) 5.5 12.3 5000.0 40.8 125.2 (0.32, 0.61) Ex.(97) Com.(4-13)5.4 11.8 5000.0 42.3 135.5 (0.33, 0.60) Ex.(98) Com.(4-14) 5.5 11.15000.0 45.0 104.8 (0.32, 0.61) Ex.(99) Com.(4-15) 5.4 11.5 5000.0 43.5104.3 (0.31, 0.60) Ex.(100) Com.(4-16) 5.5 12.1 5000.0 41.4 132.0 (0.31,0.61) Ex.(101) Com.(4-17) 5.5 11.5 5000.0 43.7 143.1 (0.31, 0.60)Ex.(102) Com.(4-18) 5.4 12.0 5000.0 41.6 120.6 (0.33, 0.61) Ex.(103)Com.(4-19) 5.5 12.1 5000.0 41.5 141.9 (0.30, 0.60) Ex.(104) Com.(4-20)5.5 11.2 5000.0 44.5 114.0 (0.31, 0.61) Ex.(105) Com.(4-21) 5.5 12.45000.0 40.3 104.5 (0.31, 0.60) Ex.(106) Com.(4-22) 5.4 11.3 5000.0 44.3132.7 (0.33, 0.61) Ex.(107) Com.(4-23) 5.4 12.1 5000.0 41.3 114.5 (0.33,0.61) Ex.(108) Com.(4-24) 5.5 12.3 5000.0 40.6 106.5 (0.30, 0.60)Ex.(109) Com.(4-25) 5.4 11.7 5000.0 42.7 139.5 (0.31, 0.61) Ex.(110)Com.(4-26) 5.5 12.0 5000.0 41.7 149.0 (0.31, 0.60) Ex.(111) Com.(4-27)5.4 12.3 5000.0 40.7 109.7 (0.33, 0.61) Ex.(112) Com.(4-28) 5.5 12.05000.0 41.6 135.6 (0.32, 0.61) Ex.(113) Com.(5-1) 5.0 9.2 5000.0 54.4141.1 (0.31, 0.60) Ex.(114) Com.(5-2) 5.4 11.8 5000.0 42.5 148.2 (0.33,0.61) Ex.(115) Com.(6-19) 5.4 10.9 5000.0 46.0 121.6 (0.30, 0.60)Ex.(116) Com.(6-20) 5.3 11.0 5000.0 45.3 138.3 (0.31, 0.61) Ex.(117)Com.(6-21) 5.3 10.8 5000.0 46.2 135.4 (0.31, 0.60) Ex.(118) Com.(6-22)5.4 11.0 5000.0 45.6 143.5 (0.33, 0.61) Ex.(119) Com.(6-23) 5.3 10.55000.0 47.6 124.1 (0.32, 0.61) Ex.(120) Com.(7-1) 5.1 9.6 5000.0 52.1107.6 (0.33, 0.60) Ex.(121) Com.(7-2) 5.1 9.8 5000.0 50.8 90.8 (0.31,0.61) Ex.(122) Com.(7-3) 5.0 9.4 5000.0 53.0 148.4 (0.31, 0.60) Ex.(123)Com.(7-4) 5.0 9.9 5000.0 50.4 105.3 (0.33, 0.61) Ex.(124) Com.(7-5) 5.511.5 5000.0 43.6 125.2 (0.32, 0.61) Ex.(125) Com.(7-6) 5.5 11.7 5000.042.8 135.5 (0.33, 0.60) Ex.(126) Com.(7-7) 5.4 10.5 5000.0 47.7 104.8(0.32, 0.61) Ex.(127) Com.(7-9) 5.4 11.3 5000.0 44.3 104.3 (0.31, 0.60)Ex.(128) Com.(7-10) 5.4 11.5 5000.0 43.5 132.0 (0.31, 0.61) Ex.(129)Com.(7-11) 5.4 11.2 5000.0 44.7 143.1 (0.31, 0.60) Ex.(130) Com.(7-12)5.4 11.6 5000.0 43.2 120.6 (0.33, 0.61) Ex.(131) Com.(7-13) 5.5 12.25000.0 40.9 141.9 (0.30, 0.60) Ex.(132) Com.(7-14) 5.5 12.2 5000.0 40.9114.0 (0.31, 0.61) Ex.(133) Com.(7-15) 5.6 12.5 5000.0 40.1 104.5 (0.31,0.60) Ex.(134) Com.(7-16) 5.5 12.3 5000.0 40.7 132.7 (0.33, 0.61)Ex.(135) Com.(7-17) 5.5 11.8 5000.0 42.5 114.5 (0.33, 0.61) Ex.(136)Com.(7-18) 5.5 11.7 5000.0 42.8 132.0 (0.31, 0.60) Ex.(137) Com.(7-19)5.5 11.7 5000.0 42.9 128.5 (0.33, 0.61) Ex.(138) Com.(7-20) 5.5 11.85000.0 42.2 92.3 (0.32, 0.61)

As shown in Table 4 above, the OLEDs using the above compounds asmaterials for a hole transport layer, have reduced driving voltage andsignificantly improved luminous efficiency and lifespan.

This is explained that the compounds of the present invention bonding anamine group with two of dibenzofurane or dibenzothiophene substituted anaryl not a heteroaryl, than the comparative compounds like comparativecompound A which is NPB, comparative compound B substituted one ofdibenzofuran, and comparative compound C and D substituted three ofdibenzofuran, have more proper HOMO and LUMO value and it is causedfaster mobility by means of improving charge balance with adjacentlayers. So, the OLEDs comprising the compounds of the present inventionwas obtained a reduced driving voltage and a improved lifespan.

Accordingly, it was shown that even with the same core, the chemicalproperties of the compounds and the element properties of the compoundsdepend on the substituent bonded to the core.

Test Example 139 Blue Organic Light Emitting Diode (Emission-AuxiliaryLayer)

Organic light emitting diodes (OLEDs) were fabricated according to aconventional method by using a synthesized compound as a hole transportlayer material. First, an ITO layer (anode) was formed on a glasssubstrate, and a film of 2-TNATA was vacuum-deposited on the ITO layerto form a hole injection layer with a thickness of 60 nm. Subsequently,a film of 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter,“NPD”) was vacuum-deposited on the hole injection layer to form a holetransport layer with a thickness of 60 nm. Subsequently, a film of thecompound 1-1 of the present invention was vacuum-deposited on the holeinjection layer to form a emission-auxiliary layer with a thickness of20 nm. Subsequently, a light emitting layer with a thickness of 30 nmwas deposited on the emission-auxiliary layer by using the9,10-di(naphthalen-2-yl)anthracene as a host material and BD-052X(produced by Idemitsu kosan) as a dopant material in a weight ratio of96:4.

Next, a film of BAlq was vacuum-deposited with a thickness of 10 nm onthe light emitting layer to form a hole blocking layer, and a film ofAlq_(a) was formed with a thickness of 40 nm to form an electrontransport layer. Next, LiF as halogenated alkali metal was depositedwith a thickness of 0.2 nm on the electron transport layer to form anelectron injection layer, and then Al was deposited with a thickness of150 nm on the electron injection layer to form a cathode. In this way,the OLED was completed.

[Test Example 140] to [Test Example 183] Blue Organic Light EmittingDiode (an Emission-Auxiliary Layer)

The OLED was manufactured in the same manner as described in TestExample 139, except that any one of the compounds 1-2 to 1-7, 2-1 to2-7, 3-1 to 3-7, 4-1 to 4-7, 6-1 to 6-5, and 7-9 to 7-20 of the presentinvention in the Table 5 below was used as the emission-auxiliary layermaterial, instead of the inventive compound 1-1.

Comparative Example 5 Blue Organic Light Emitting Diode (anEmission-Auxiliary Layer)

An OLED was manufactured in the same manner as described in Test Example139, except not to form the emission-auxiliary layer.

Comparative Example 6 Blue Organic Light Emitting Diode (anEmission-Auxiliary Layer)

An OLED was manufactured in the same manner as described in Test Example139, except that Comparative Compound B represented below was used asthe emission-auxiliary layer material, instead of the inventive compound1-1.

Comparative Example 7 Blue Organic Light Emitting Diode (anEmission-Auxiliary Layer)

An OLED was manufactured in the same manner as described in Test Example139, except that Comparative Compound C represented below was used asthe emission-auxiliary layer material, instead of the inventive compound1-1.

Comparative Example 8 Blue Organic Light Emitting Diode (anEmission-Auxiliary Layer)

An OLED was manufactured in the same manner as described in Test Example139, except that Comparative Compound D represented below was used asthe emission-auxiliary layer material, instead of the inventive compound1-1.

A forward bias DC voltage was applied to each of the OLEDs manufacturedthrough Test Examples 139 to 183 and Comparative Example 5 to 8, andelectro-luminescence (EL) characteristics of the OLED were measured byPR-650 (Photoresearch). Also, T95 life span was measured by life spanmeasuring equipment (Mcscience) at a reference brightness of 5000 cd/m².Table 5 below shows evaluation results of OLEDs manufactured TestExamples and Comparative Examples.

TABLE 5 Current Voltage Density Brightness Efficiency Lifetime Compound(V) (mA/cm²) (cd/m²) (cd/A) T(95) Com. Ex(5) — 5.3 11.1 500.0 4.5 63.2Com. Ex(6) Com. Com. B 5.6 8.2 500.0 6.1 85.1 Com. Ex(7) Com. Com. C 5.77.3 500.0 6.9 84.9 Com. Ex(8) Com. Com. D 5.8. 7.5 500.0 6.7 84.7Ex.(139) Com.(1-1) 5.4 3.9 500.0 12.9 94.9 Ex.(140) Com.(1-2) 5.2 4.0500.0 12.5 104.0 Ex.(141) Com.(1-3) 5.3 3.9 500.0 12.9 137.8 Ex.(142)Com.(1-4) 5.5 4.9 500.0 10.3 133.4 Ex.(143) Com.(1-5) 5.3 4.7 500.0 10.7118.9 Ex.(144) Com.(1-6) 5.4 4.8 500.0 10.5 114.3 Ex.(145) Com.(1-7) 5.24.2 500.0 11.8 113.3 Ex.(146) Com.(2-1) 5.2 5.6 500.0 8.9 114.2 Ex.(147)Com.(2-2) 5.2 5.9 500.0 8.4 132.8 Ex.(148) Com.(2-3) 5.3 6.1 500.0 8.2108.6 Ex.(149) Com.(2-4) 5.3 6.0 500.0 8.3 137.0 Ex.(150) Com.(2-5) 5.45.8 500.0 8.6 134.6 Ex.(151) Com.(2-6) 5.3 5.7 500.0 8.7 122.1 Ex.(152)Com.(2-7) 5.2 6.2 500.0 8.1 103.0 Ex.(153) Com.(3-1) 5.5 4.7 500.0 10.6130.6 Ex.(154) Com.(3-2) 5.4 4.0 500.0 12.6 115.6 Ex.(155) Com.(3-3) 5.34.3 500.0 11.7 138.9 Ex.(156) Com.(3-4) 5.2 4.8 500.0 10.5 116.2Ex.(157) Com.(3-5) 5.2 4.5 500.0 11.1 113.4 Ex.(158) Com.(3-6) 5.3 4.8500.0 10.5 136.5 Ex.(159) Com.(3-7) 5.4 4.1 500.0 12.1 105.4 Ex.(160)Com.(4-1) 5.4 5.6 500.0 8.9 136.4 Ex.(161) Com.(4-2) 5.5 5.8 500.0 8.6115.3 Ex.(162) Com.(4-3) 5.4 5.7 500.0 8.8 123.5 Ex.(163) Com.(4-4) 5.45.6 500.0 8.9 132.1 Ex.(164) Com.(4-5) 5.3 5.7 500.0 8.7 135.4 Ex.(165)Com.(4-6) 5.3 5.6 500.0 8.9 126.7 Ex.(166) Com.(4-7) 5.3 5.6 500.0 9.0129.1 Ex.(167) Com.(6-1) 5.2 5.4 500.0 9.2 138.0 Ex.(168) Com.(6-2) 5.35.0 500.0 10.0 116.0 Ex.(169) Com.(6-3) 5.5 5.2 500.0 9.7 138.4 Ex.(170)Com.(6-4) 5.5 5.2 500.0 9.6 119.1 Ex.(171) Com.(6-5) 5.5 5.4 500.0 9.2114.2 Ex.(172) Com.(7-9) 5.4 3.4 500.0 14.8 124.7 Ex.(173) Com.(7-10)5.3 3.4 500.0 14.6 103.2 Ex.(174) Com.(7-11) 5.5 3.4 500.0 14.9 115.4Ex.(175) Com.(7-12) 5.3 3.4 500.0 14.7 137.7 Ex.(176) Com.(7-13) 5.4 3.9500.0 13.0 118.8 Ex.(177) Com.(7-14) 5.5 3.9 500.0 12.8 121.9 Ex.(178)Com.(7-15) 5.3 3.9 500.0 12.9 113.8 Ex.(179) Com.(7-16) 5.3 4.1 500.012.3 105.7 Ex.(180) Com.(7-17) 5.4 3.7 500.0 13.5 130.1 Ex.(181)Com.(7-18) 5.5 3.8 500.0 13.1 127.5 Ex.(182) Com.(7-19) 5.4 3.6 500.013.8 114.5 Ex.(183) Com.(7-20) 5.5 3.6 500.0 13.7 134.6

As shown in Table 5 above, the OLEDs using the above compounds asmaterials for the emitting auxiliary layer, has significantly improvedluminous efficiency and lifespan compared to the OLEDs of thecomparative Examples which don't form the emitting auxiliary layer, buthas similar driving voltage.

Also, in the case where the OLEDs using the compounds of the presentinvention bonding an amine group with two of dibenzofurane ordibenzothiophene substituted an aryl not a hetero aryl were used asmaterials for the emitting auxiliary layer than the OLEDs usingcomparative compound B substituted one of dibenzofuran, and comparativecompound C and D substituted three of dibenzofuran, significantlyimproved luminous efficiency and a lifespan was obtained.

This is, when the compounds of the present invention were used as theemitting auxiliary layer, deep HOMO energy level what is inherentproperties of the compound of the present invention was caused a chargebalance of between hole and electron in the lighting emitting layer dueto move suitable amounts of the hole from in a hole transport layer to alighting emitting layer, and also efficiency and lifespan were improvedbecause of that the high T1 value block the movement of electrons fromthe light emitting layer to the hole transport layer and prevent theemission to interface of the hole transport layer.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment. The scope of thepresent invention shall be construed on the basis of the accompanyingclaims, and it shall be construed that all of the technical ideasincluded within the scope equivalent to the claims belong to the presentinvention.

1. An organic electric element, comprising: a first electrode, a second electrode, and a light emitting layer disposed between the first electrode and the second electrode, the organic electric element comprises an organic material layer disposed between the first electrode and the light emitting layer, the organic material layer comprising a compound represented by Formula 1,

wherein, X and Y are independently O or S, Ar¹ and Ar² are each independently selected from the group consisting of a C₆-C₆₀ aryl group, a fluorenyl group or combinations thereof, q is an integer of 1 or 2, Ar¹ and Ar² may be the same or different when q is 2, L is selected from the group consisting of a C₆-C₆₀ arylene group, a fluorenylene group, a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring, or a C₂-C₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, R¹ to R⁴ are i) each independently selected from the group consisting of hydrogen, deuterium, halogen, a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring, C₁-C₅₀ alkyl group, C₂-C₂₀ alkenyl group, C₂-C₂₀ alkynyl group, C₁-C₃₀ alkoxy group, C₆-C₃₀ aryloxy group, -L′-N(R^(a)) (R^(b)) or combinations thereof, or ii) at least one of adjacent R¹s to R⁴s may optionally form ring, herein, when R¹ to R⁴ don't form ring, R¹ to R⁴ are the same as defined above, and m and n are each an integer from 0 to 4, o and p are each an integer of 0 to 3, when m, n, o and p are each an integer of 2 or more, each of plural R¹s, R²s, R³s and R⁴s may be the same or different, L′ is selected from the group consisting of a single bond, a C₆-C₆₀ arylene group, a fluorenylene group, a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring, or C₂-C₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, R^(a) and R^(b) may be each independently selected from the group consisting of a C₆-C₆₀ aryl group, a fluorenyl group, a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring, and a C₂-C₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, and, with the provisos that when Ar¹ and Ar² are an aryl group or a fluorenyl group, Ar¹ and Ar² are each optionally substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted by deuterium, a fluorenyl group, a C₃-C₂₀ cycloalkyl group, a C₇-C₂₀ arylalkyl group, and a C₈-C₂₀ arylalkenyl group, when L is an arylene group, a fluorenylene group, a fused ring group or hetero cyclic group, L is optionally substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted with deuterium, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C₃-C₂₀ cycloalkyl group, a C₇-C₂₀ arylalkyl group, and a C₈-C₂₀ arylalkenyl group, when R¹ to R⁴ are an aryl group, a fluorenyl group, a hetero cyclic group, a fused ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, or an aryloxy group, R¹ to R⁴ are each optionally substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted with deuterium, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C₃-C₂₀ cycloalkyl group, a C₇-C₂₀ arylalkyl group, and a C₈-C₂₀ arylalkenyl group.
 2. The organic electric element as claimed in claim 1, wherein Formula 1 is represented by Formula 2 to Formula 5:

wherein, X, Y, Ar¹, Ar², L, R¹ to R⁴, m, n, o, p and q are the same as defined in claim
 1. 3. The organic electric element as claimed in claim 1, wherein Formula 1 is represented by Formula 6 or Formula 7:

wherein, X, Y, Ar¹, Ar², L, R¹ to R⁴, m, n, o and p are the same as defined in claim
 1. 4. The organic electric element as claimed in claim 1, wherein Formula 1 is selected from the following compounds:


5. The organic electric element as claimed in claim 1, wherein the organic material layer comprises at least one layer of a hole injection layer, a hole transport layer, or a emission-auxiliary layer containing the compound represented by Formula 1, wherein the compound is the same kind or two or more different kinds.
 6. The organic electric element as claimed in claim 1, wherein the organic electric element further includes at least one layer to improve luminous efficiency which is formed on at least one of the sides the first and second electrodes, which is opposite to the organic material layer.
 7. The organic electric element as claimed in claim 1, wherein the organic material layer is formed by any one of the processes of spin coating, nozzle printing, inkjet printing, slot coating, dip coating and roll-to-roll.
 8. An electronic device comprising a display device, which comprises the organic electric element as claimed in claim 1, and a control unit for driving the display device.
 9. The electronic device of claim 8, wherein the organic electric element comprises at least one of an organic light emitting diode, an organic solar cell, an organic photo conductor, an organic transistor, and an element for monochromatic or white illumination. 